


Perky and Plump

by justanotherbusyfangirl



Series: Holiday Thongs [3]
Category: Supernatural
Genre: Dean's Ass, F/M, Male Thong, Vaginal Sex
Language: English
Status: Completed
Published: 2017-12-21
Updated: 2017-12-21
Packaged: 2019-09-03 00:11:33
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,764
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16797532
Author URL: https://archiveofourown.org/users/justanotherbusyfangirl/pseuds/justanotherbusyfangirl
Summary: Dean decides to show you how good your present looks on him.





	Perky and Plump

You weren’t super happy about it, but your little dysfunctional family wasn’t going to make it home to the bunker for Christmas. 

The case was too complicated, twists and turns at every little new bit of information that made it take longer to catch the monster than you’d expected. Plus, you were at least a three day drive away. You decided you may as well have a motel-room holiday celebration in the small town, taking a few days rest once the case finished up.

You went to Sam and Dean’s room for the celebration, bearing gifts that you’d bought in the town. None of the presents the three of you exchanged were any level of serious, but it was the act of giving that mattered, right?

For Sam, you found a men’s grooming set, travel sized but including anything and everything he would ever need to keep his hair _just right_. Dean cackled at the gift, making fun of his brother’s locks for the billionth time, but you saw Sam’s slight pleasure at your gift in his eye. The two of you shared a smile before you handed Dean his present.

“If you thought you could make fun of Sam for his gift…” you said to Dean, leaving the sentence hanging to insinuate that Sam would definitely be able to make fun of Dean.

Dean pulled the paper open, excited at the idea of getting a gift.

When he held the red, Santa-themed thong up, you and Sam lost it. Dean was in shock at the gift to the point that he didn’t say anything initially, letting you and Sam roll in laughter. Finally Dean’s brain caught up to his mouth and he grinned cockily, joining in on your laughter.

“Let’s set up a runway in here, I’ll model this puppy for y’all,” he said, laughing harder.

“No, bro! Nobody wants to see that!” Sam said, hands up in the air to shield him from the image of Dean in the thong. “Too much, too much!”

You just laughed, the thought of Dean in the thong having been on your mind ever since you bought it. Unfortunately, even though it was a gag gift, you figured it had to look good on him.

The three of you drank eggnog well into the evening, the crappy motel television in the corner showing old holiday movies in the background. It was turning out to be a pretty decent Christmas, even though you wished you were home in the bunker.

When it was getting late enough, you grabbed your things to head back to your room, glad that you’d been able to find a motel with more than one vacancy.

“Night, boys,” you said, heading to the door. “Merry Christmas and I’ll see you in the morning.”

Sam waved your way, his eyes eggnog-hazy and half closed. Dean followed you to the door, opening it for you. “Hey, Y/N,” he said, his gaze rising to the top of the doorway. You followed his eyes, seeing that the motel had hung sprigs of fake mistletoe above the doorways. The cocky grin on his face made you roll your eyes, knowing that he was egging for a free make-out session.

“You wish, Winchester,” you replied, standing on your tiptoes to kiss his cheek innocently, turning toward your room before he could see the blush that landed on your face. You slipped into your room quickly as he closed his own door, deciding to shower before you headed to bed.

The hot water pressure was surprisingly good in the motel, so you spent a little bit of time in the shower. You soaped and lathered your body, taking the time to shave and pamper yourself as a Christmas treat. 

When you headed back into the room, you pulled on one of Dean’s flannel shirts that you’d stolen from him and nothing else, crawling into bed. You flipped the television on, not quite tired enough to sleep but figuring that a boring, predictable holiday movie could lull you into dreamland.

Before you could even get settled, there was a knock on your door. You rolled your eyes, wondering what the Winchesters were up to now. You headed for the door, opening it a crack to not give the world outside too much of a view of your bare legs.

“Let me in, Y/N,” Dean said, pushing the door open. You rolled your eyes but let him in, closing the door behind him. Dean took a couple paces to look at your television, distracting himself long enough that you went back to where you’d been sitting comfortably in your bed. You criss-crossed your legs and pulled the covers up to cover them, suddenly all too aware of the fact that you hadn’t put underwear on after your shower.

“Couldn’t sleep,” Dean finally said, turning toward you and sitting on the edge of the bed. “Plus, Sammy’s snoring up a storm in there…”

You laughed, doubly glad that you’d gotten your own room. You noticed that Dean’s hair was damp, indicating that he, too, had taken a shower since you left their room. “I’m afraid I’m not going to be too entertaining either, Dean. I was heading to sleep myself.”

Dean scoffed and looked away, something uncertain behind his eyes. “What’s up, Dean?” you asked, knowing that he hadn’t just come to your room to get away from Sam’s snoring.

Dean looked at you, studying you for a moment. His eyes traced over your damp hair then to the flannel shirt you were wearing, seeing that it was his shirt. His eyes widened slightly before he cleared his throat, confidence seeping back onto his face.

“Got something to show you, Y/N,” Dean said, standing up suddenly and smiling his classic, cocky smile. “I mean, I don’t think you realized it…” Dean’s hands were at his belt, undoing the buckle deftly. When he moved to his button and zipper, you sat up, unsure of what he was doing.

“Dean-“ you began to interrupt, but his eyes darted back over to meet yours and stopped the words in your throat. You gulped as you saw the teasing and arousal there, wanting to know exactly what he was planning.

“..but my ass,” Dean continued, pulling his jeans down so that you could see the red with white fuzz, “looks _damn fine_ in a thong.”

Dean let his jeans fall down his thighs to catch at his knees and he turned slightly away from you, giving you a full view of him in his Santa-themed thong you’d gifted him. Your eyes widened, a shocked expression on your face.

You looked back up at his face, wanting more of an explanation for him suddenly baring himself to you. Dean’s eyebrows were raised, waiting for your response. Without your permission, your eyes trailed back down to his butt, taking in the full picture as he was silently encouraging you to do.

He was right.

Dean had a fantastic butt. Sure, you’d oogled it before, but that was always through jeans. This was an unhindered view of his lily-white ass, perky and plump, practically asking to be squeezed. The red material of the thong circled it nicely, disappearing into the crease between his cheeks and making it look even bigger than it probably was.

“Well, don’t you agree?” Dean finally said, making you realize that he was watching you stare at him.

You gulped, squeezing the comforter that was laying over your legs tightly in your hands. Checking out Dean’s butt in that thong had sent heat between your legs and your heartbeat was definitely beating harder than before.

“Yeah, Dean,” you tried to say casually. “Damn fine ass you have there.”

You thought you pulled off the casual talk, but Dean didn’t seem to buy it. He kicked his shoes off and let his jeans fall the rest of the way off, turning to show you the whole picture. “I mean, the back looks good, for sure, and the front looks good too,” he said, his hands motioning toward his bulge as he faced you. You were sure your face was beet red as your eyes looked at the front of the thong, the outline of his cock and balls pretty easy for you to see. _Was he semi-hard?_ you found yourself wondering, but you wouldn’t let yourself look closer to find out.

“Dean, what are you doing?” you finally asked, gulping in nervousness at his potential answer.

Dean heard the nervousness in your voice and you saw the instant that he stepped out of his cocky persona. He sat back on the edge of the bed and put his hand lightly on your knee over the covers.

“Look, Y/N/N,” he said, his voice soothing and serious. “All joking aside, I, uh, like you and think you like me, too. If you want to try…” Dean waved his hand between the two of you, not putting into words what he was insinuating. “Just say the word. If not, I’ll put my jeans back on and we can forget this ever happened.”

You watched Dean, seeing the nerves flit across his face as he waited for your response.

“I don’t think I could ever forget that ass, Dean,” you finally said, smiling. “Come here, dork.”

You pulled Dean by his shirt toward you, pressing your lips to his. Dean smiled into the kiss before moving closer to you, getting onto all fours to position himself above your body. You uncrossed your legs beneath the covers so that he could lower his body onto yours, his two shirts and the comforter between you.

As Dean took over the kiss, his tongue exploring your mouth, your hands wrapped around his body. For as many times as you’d admired Dean’s physique, this was the first time you’d been allowed to touch, so you were damn sure to get your fill. Your hands started at his shoulder blades, moving slowly down his back.

You’d nearly forgotten about the thong Dean was wearing as your hands landed on his bare butt. You gathered his cheeks in your hands and squeezed, earning a moan from Dean’s lips.

“You keep that up, we’re going somewhere, Y/N,” Dean mumbled, moving his lips to your ear. He bit the lobe gently before kissing his way down your neck.

“Maybe I want to go somewhere, Dean,” you replied, tilting your head to give him more room to work. At that confession, Dean bucked his hips down against the comforter, letting you feel the flex of his ass as he did so. You squeezed the skin again, groaning as he began a steady thrust against your body.

“Dean…” you whimpered, all the heat in your body seeming to pool between your legs. You needed the comforter gone, now.

Dean understood your plea, rising up just enough to move the bedding to the side. He settled back between your legs, gazing down at you with a look you never thought you’d be on the receiving end of. “Gorgeous…” he breathed before kissing you again. Your arms and legs wrapped around his body, pulling the bulge of his ridiculous Santa thong against your uncovered core. Dean propped himself up using one arm, letting his other hand roam down your body.

He gripped your bare thigh, holding it tight as he ground into you. You were grateful that you’d taken your pampering shower as he slid his hand up your smooth leg, inching his fingers beneath his shirt that you were wearing.

When he was holding your hip and hadn’t met the resistance of fabric, he broke the kiss. “Are you not wearing underwear?” he asked incredulously, his fingers beginning to explore.

You blushed as you grinned, shaking your head. “I was going to bed, Dean,” you explained before biting your lip.

Dean’s hand reached around to grab a handful of your ass, grounding his now completely hard, thong-covered cock into your core. “Fuck, Y/N, you’re going to kill me here.”

Your giggle turned into a moan of his name as he moved slightly and thrust against you again, his cock lining up perfectly to rub against your clit. “Dean, please…”

“Yeah, okay,” he said, pulling away and looking down at you. His shirt was now riding up your stomach, giving him the full view of your uncovered pussy. “Fuck…” he whispered as he pulled his shirt over his head, reaching down to take yours off as well. 

When your shirts were off, Dean stayed on his knees, gazing down at your nude form. You did everything in your power to not cover yourself up, letting him take his fill of you, but then your eyes trailed down his body. The predatory look in Dean’s eyes was nearly enough to distract you from the ridiculous Santa thong, but in the end you couldn’t stop the giggle that escaped your lips.

“Wha-“ Dean asked, having obviously forgotten about what he was wearing. He looked down and realized the picture he made, his hard cock pressing against the red fabric. “You’re never going to let me live this down are you…” he mumbled, tearing the underwear off and settling between your legs.

“I think we need to thank that thong,” you commented before Dean took control of your mouth once more, his hand sliding between your legs to tease at your folds. He slipped a finger inside of you, pumping twice before adding a second. You were wet enough that he met no resistance, his thumb finding your clit and rubbing it in time with his fingers. 

“Dean, please,” you got out between kisses, reaching down for his erection. You pushed his hand out of the way, rubbing the head of his cock along your pussy to wet it with your slick. You notched it at your entrance, shifting your hips slightly to catch him inside of you.

Dean stopped your kiss, looking into your eyes as he pressed his hips forward, sheathing himself in your heat. “So tight,” he hissed, stopping only when he was balls deep inside of you.

Your legs wrapped around Dean’s waist, making sure he wasn’t going anywhere. He nuzzled his face into your neck, beginning to lave kisses and nips along your neck and shoulder as his hips started to move. You were already worked up and your hands were exploring once more, ensuring that you were not going to last very long before Dean would draw an orgasm from you. Dean positioned his hips so that every thrust had him dragging along your clit.

Your fingers dug into Dean’s back as you held on, feeling his firm muscles flex with every move. Dean was mumbling praises against your skin, his hand finding its place on your leg again to keep you right where he wanted.

“Fuck, Y/N, so incredible…” Dean groaned, hips speeding slightly. “Tight, fuck… you’re perfect you know that?”

“Dean…please…” was all you could respond, making him shift slightly with determination. The new position had Dean hitting just the right spot inside of you, your body responding almost immediately.

Dean didn’t let up until you were crying his name, body clenching beneath him as you came. He kept moving, his cock working you through your high until he followed you, spilling deep inside with a moan of your name.

Dean finally stilled, his whole body pressed against yours, sweat on his skin and yours. He breathed hard for a minute before pulling out of you, rolling over to lay on the bed next to you. Without hesitating, he pulled you into his body, his arm wrapped around you and holding you close.

“Damn…” he said, still catching his breath. 

“Yeah,” you agreed, not knowing exactly what to say. You hoped that things weren’t going to get weird, now that you had slept with Dean. What if he regretted it, what if this ruined your hunting partnership, what if he and Sam left you?

“I’m definitely getting that thong back out for you next Christmas, if that’s what happens because of it,” Dean finally said, hint of a joke in his voice but otherwise serious. You relaxed, realizing that if Dean was already planning something for the two of you a year away, this wasn’t just a one-time thing.

“Maybe I’ll buy you a new one for Valentine’s Day,” you shot back, earning a chuckle. Dean kissed your forehead.

“Sounds perfect,” he mumbled, pulling at the comforter until you were both covered and snuggled together, falling easily to sleep.


End file.
